With celebrity couples breaking up on the reg, it’s hard to keep track of who dated whom. From flings to the then-real thing, click through to see 20 celeb couples that will make your jaw drop.

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Is Ashton Kutcher a mad man?! The couple dated from 1998-2001, but January Jones called it quits because she claims he didn’t believe in her. "He was not supportive of my acting,” the Mad Men actress spilled to GQ. “He was like, 'I don't think you're going to be good at this.' So, f--- you!" Jones proved him wrong!

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Is Nick Lachey the reason for Kim Kardashian’s success? Before becoming Mrs. West, the reality star dated Nick Lachey after his divorce from Jessica Simpson. But her intentions may have been to find fame, not love. "Let’s just say this: We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside," he told Details.

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If you had to guess Ryan Gosling’s two great loves, would Sandra Bullock be one of your choices? "I had two of the greatest girlfriends of all time. I haven't met anybody who could top them," Gosling told The Times about Sandra Bullock and Rachel McAdams. The swoon-worthy star dated Bullock from 2002 to 2003 after meeting her on the set of the flick Murder by Numbers.

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Before Justin Timberlake said “Bye, Bye, Bye” to Britney Spears, he dated another famous singer. "Justin and I would go out together and have fun and make out," Fergie spilled to Cosmopolitan. "But we were never serious. He was Mr. Right Now."

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It’s hard to remember an ex of Brad Pitt’s who isn’t Jennifer Aniston. But it was Christina Applegate who broke the actor's heart in 1989. "We went to the MTV Movie Awards and I ditched him! I left him there and I felt really bad about it, I really, really do. I left with somebody else!" We bet she regrets that decision!

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Opposites don’t always attract! Rumors circulated in 2007 that Rihanna and Shia LaBeouf were an item. It took LaBeouf two years to finally dish about the not-so-hot romance. “It never got beyond one date,” he told Playboy. “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”

Did Vanilla Ice really think Madonna was “Like a Virgin”? After dating for eight months in 1990, the rapper ended it because of her book, Sex. "But I broke up with her after she printed that book because I was hurt to be an unwitting part of this slutty package," he confessed. "It was disgusting and cheap. We were in a relationship yet it looked like she was screwing all these other people."

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Scarlett Johansson and Blake Lively weren’t the only girls Ryan Reynolds planned to tie the knot with. After meeting Alanis Morissette at Drew Barrymore’s birthday in 2002, the duo got engaged after two years of dating. Despite a broken engagement, Morissette wished Ryan Reynolds well during an interview with Access Hollywood in 2008.

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Could Drew Barrymore and Christian Bale have been the Brangelina of Hollywood? The A-list celebs dated in their teens, but the Dark Knight star didn’t impress Barrymore. “We went to see some bloody awful horror film, and that was the end of it,” Bale confessed to GQ Australia. "She never called again."

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It was definitely a happy new year for George Clooney and Lucy Liu. After rumors of a romance began to surface, the actors were spotted ringing in 2006 with a steamy midnight kiss.

Cougar Alert! After meeting on the set of the comedy Something’s Gotta Give, Keanu Reeves reportedly left girlfriend Lynn Collins for Diane Keaton. But that’s not the shocking part. Keaton is about 20 years his senior!

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Out of all the men Cher dated, Tom Cruise is one of her all-time favorites in bed. “He was in the top five,” the singer said. “It’s not a long list, just a good list.”

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Currently married to Kristen Bell, Dax Shepard was linked to another blonde before settling down. Shepard and Kate Hudson briefly dated in 2007 following Hudson’s split from Owen Wilson.

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Ms. GOOP found love with actor Luke Wilson about a year before she tied the knot with rocker Chris Martin. What the what?! Although Paltrow and Wilson seem like complete opposites, they dated for an entire year before parting ways.

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Love was in the air when Sarah Jessica Parker and Robert Downey Jr. dated in the 1980s, but Downey’s addiction to drugs and alcohol at the time ended the romance. "I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica, because it is the furthest thing from what she is," he told Parade.

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Sparks flew on the set of The Fresh Prince of Bel-Air when Tyra Banks joined the cast as Will Smith’s girlfriend. The actors took their relationship off-screen, as they were rumored to have dated from 1993 to 1994.

Jake Gyllenhaal and Natalie Portman dated in 2006 and seemed to have left off on good terms after he presented her with an award for her role in the thriller Black Swan. "The Audrey Hepburn of our generation. She's graceful, has amazing eyebrows, and is talented, really short, funny, smart, dedicated, incredibly kind and Jewish!"

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After Julia Roberts guest-starred on Matthew Perry’s show Friends in 1996, the actor snagged a few dates with America’s Sweetheart before the duo parted ways.

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The actors didn’t just have a fling; they dated for almost four years! Unfortunately, they called it quits in 2000.